Sodium hydride → 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

7-Iodo-1H-pyrazolo[4,3-b]pyridine (0.77 g, 3.14 mmol) and sodium hydride (0.151 g, 3.77 mmol) were combined in DMF (31.4 ml) and stirred for 10 minutes and cooled to 0° C. 1-(Chloromethyl)-4-methoxybenzene (0.449 ml, 3.30 mmol) was added and the reaction was allowed to stir at room temperature for 1 hour. The reaction mixture was poured into ice water (200 mL) containing saturated ammonium chloride (50 mL) and extracted with ethyl acetate (2×50 mL). The organics were separated and dried over sodium sulfate, filtered, and absorbed onto silica gel. Column chromatography with hexanes/ethyl acetate (0-50%) gave the products 7-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine and 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine as a 6:4 mixture of isomers (0.9 g, 78%). MS [M+H] found 366.1.

Provenance & Evidence